[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

WO1999002041A1 - Satiety product - Google Patents

Satiety product Download PDF

Info

Publication number
WO1999002041A1
WO1999002041A1 PCT/SE1998/001326 SE9801326W WO9902041A1 WO 1999002041 A1 WO1999002041 A1 WO 1999002041A1 SE 9801326 W SE9801326 W SE 9801326W WO 9902041 A1 WO9902041 A1 WO 9902041A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
food
emulsifier
triglyceride oils
composition according
Prior art date
Application number
PCT/SE1998/001326
Other languages
English (en)
French (fr)
Inventor
Bengt Herslöf
Lars Lindmark
Karin Bohlinder
Anders Carlsson
Original Assignee
Scotia Holdings Plc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to DK98934040T priority Critical patent/DK0994655T3/da
Priority to IL13348598A priority patent/IL133485A/en
Application filed by Scotia Holdings Plc filed Critical Scotia Holdings Plc
Priority to BR9810674-0A priority patent/BR9810674A/pt
Priority to AU83647/98A priority patent/AU747540B2/en
Priority to KR1020007000090A priority patent/KR100597221B1/ko
Priority to DE69828789T priority patent/DE69828789T2/de
Priority to AT98934040T priority patent/ATE287647T1/de
Priority to HU0003122A priority patent/HU229831B1/hu
Priority to EA200000099A priority patent/EA003833B1/ru
Priority to EEP200000011A priority patent/EE03994B1/xx
Priority to EP98934040A priority patent/EP0994655B1/en
Priority to PL338086A priority patent/PL191304B1/pl
Priority to US09/462,330 priority patent/US6517883B1/en
Priority to CA002294251A priority patent/CA2294251C/en
Priority to NZ501762A priority patent/NZ501762A/en
Priority to JP2000501655A priority patent/JP3653225B2/ja
Publication of WO1999002041A1 publication Critical patent/WO1999002041A1/en
Priority to IS5308A priority patent/IS5308A/is
Priority to NO20000046A priority patent/NO317044B1/no
Priority to HK01102061A priority patent/HK1031302A1/xx

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1315—Non-milk proteins or fats; Seeds, pulses, cereals or soja; Fatty acids, phospholipids, mono- or diglycerides or derivatives therefrom; Egg products
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0053—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/011—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/08—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing cocoa fat if specifically mentioned or containing products of cocoa fat or containing other fats, e.g. fatty acid, fatty alcohol, their esters, lecithin, paraffins

Definitions

  • the present invention refers to a mixture or an emulsion of a lipid with a polar lipid emulsifier which after ingestion gives an improved feeling of satiety and also results in reduced calorie and especially fat intake at a subsequent meal.
  • Prior art EP 0 246 294 refers to an enteric preparation for the treatment of obesity.
  • Said enteric preparation is a capsule, a tablet or microcapsules coated with a coating resistant to gastric juice which dissolves in the intestines.
  • the enteric preparation contains specific hydrophobic substances which are said to give a reduced food intake when brought into contact with the distal part of the small intestine.
  • WO 95/20943 describes the use of DGDG-rich material, a galactolipid material, as an emulsifier in oil-in-water emulsions for pharmaceutical, nutritional and cosmetic use.
  • the galactolipid material utilized in said applications was prepared from cereals by extraction of the lipids with ethanol and a subsequent purification on a chromatographic column to pure DGDG or a DGDG-rich fraction of polar lipids.
  • the emulsion can be used as a carrier in pharmaceutical compositions as well as in nutritional, cosmetical, food and agricultural products.
  • WO 97/11141 describes a method for producing a fractionated vegetable oil which is characterized by containing 10-90 % by weight of polar lipids, preferably 20-75 %, and a remainder of non-polar lipids.
  • the fractionated vegetable oil is preferably also characterized by containing more than 5 % by weight, preferably more than 20 %, glycolipids.
  • Said fractionated vegetable oil also preferably contains more than 3 % by weight, preferably more than 15 %, DGDG and consists of a wide range of polar and amphiphilic lipids in a continuous triglyceride phase.
  • the fractionated vegetable oil can be used as a surface active agent for the formulation of a food, pharmaceutical, skin care or other product for oral, enteral, parenteral, topical or any other form of administration.
  • the present invention is related to the use of a mixture or an oil-in-water emulsion of a lipid as a food or for the formulation of a food composition giving a rapid, improved and prolonged feeling of satiety, reducing calorie intake at later meals and selectively producing a greater reduction in fat consumption.
  • the invention refers to a food composition giving a prolonged feeling of satiety, comprising a mixture of triglyceride oils having a solid fat content at ambient to body temperature and a food emulsifier.
  • the invention also refers to a food composition giving a prolonged feeling of satiety, comprising an oil-in-water emulsion of triglyceride oils having a solid fat content at ambient to body temperature with a food emulsifier in an aqueous solution.
  • the triglyceride oils of said mixtures or emulsions can be any triglyceride material having a solid fat content at ambient to body temperature.
  • the triglyceride oils are defined by the percentage of solid fat content, determined by NMR serial measurements as described in IUPAC method no. 2.150, 7th edition.
  • Triglyceride refers to triacylglycerol, that is glycerol esterified to three fatty acids.
  • the triglyceride oils are preferably selected from the group consisting of palm oil, cocoa butter or other confectionery fats. Further examples of triglyceride oils are illipe butter, shea butter, kokum butter, sal butter or other natural oils or fractions thereof with a similar solid fat content or melting range. Other examples of such oils are hydrogenated or partly hydrogenated soybean oil, rapeseed oil, cotton oil and sunflower oil or fractions thereof.
  • the triglyceride oils may also be synthetic or semi-synthetic.
  • Body temperature is the temperature of the healthy human or animal body.
  • the triglyceride oils should contain at least 90 % by weight of triglycerides, preferably more than 95 % by weight.
  • the invention especially refers to a food composition wherein the triglyceride oils are a fraction of palm oil.
  • This fraction of palm oil is obtained from commercial palm oil, which is fractionated to specific mixtures of suitable triglycerides, based on the combination of mainly palmitic, oleic, linoleic and stearic esters of glycerol, respectively.
  • the content of triglycerides in the palm oil fraction should be not less than 99 % by weight.
  • the purity can be checked by conventional chromatographic methods, such as thin-layer chromatography or high-performance liquid chromatography.
  • Food emulsifiers that is emulsifiers commonly used in food applications are generally esters composed of a hydrophilic and a lipophilic part.
  • the lipophilic part is composed of stearic, palmitic, oleic, or linoleic acid or a combination of said fatty acids.
  • the hydrophilic part is generally composed of hydroxyl, carboxyl, or oxyethylene groups.
  • Examples of families of food-grade emulsifiers are lecithins, mono- and diglycerides, propylene glycol monoesters, lactylated esters, polyglycerol esters, sorbitan esters, ethoxylated esters, succinylated esters, fruit acid esters, acetylated mono- and diglycerides, phosphated mono- and diglycerides and sucrose esters.
  • the emulsion of the triglyceride oils can also be obtained when the oils are mixed with suitable foods or food products, making use of the inherent emulsification properties of said foods or food products.
  • Food emulsifiers according to the invention should be able to emulsify more than 20 % by weight of the triglyceride oils, preferably more than 40 % by weight, giving an emulsion which is still liquid in order to facilitate the processing of a food product in which the emulsion is incorporated.
  • a preferred emulsifier of the invention is lecithin, for instance produced from egg yolk, milk, soybean oil, sunflower oil, and rapeseed oil, which consists of a mixture of mainly phospholipids, such as phosphatidylcholine and phosphatidyl- ethanolamine.
  • Lecithin refers in this context to crude mixtures of said phospholipids which are obtained on degumming of the starting materials, and which are commercially available as food emulsifiers.
  • Another preferred emulsifier is a galactolipid based emulsifier.
  • Galactolipids belong to the group of glycolipids, well known constituents of plant cell membranes.
  • the most important classes of these contain one to four sugars linked glycosidically to diacylglycerol.
  • the two most abundant classes contain one and two galactose units, respectively, and the commonly used nomenclature and abbreviations of these are mono- and digalactosyldiglyceride, MGDG and DGDG, sometimes referred to as galactolipids.
  • Galactolipids primarily DGDG and DGDG-rich materials, have been investigated and found to be a surface active material of interest in industrial applications such as food, cosmetics, and pharmaceutical products.
  • Galactolipid emulsifiers are described in WO 95/20943 and WO 97/11141.
  • the invention also refers to a food product wherein the triglyceride oils are combined with other lipids containing essential fatty acids.
  • Essential fatty acids are polyunsaturated acids of the (n-6) and (n-3) families which are essential for life and good health.
  • the other lipids containing essential fatty acids can be derived from vegetable oils of all types, such as oils from the seeds and beans of soybean, sunflower, safflower, cottonseed, rapeseed (canola) , palm, palmkernel, coconut, corn, evening primrose, borage, groundnut, sesame, and similar, furthermore animal oils and fats such as fish oils, liver oils, egg oils, and similar, obvious to a person skilled in the art, which in combination with the triglycerides can be emulsified by the emulsifiers of the invention.
  • vegetable oils of all types such as oils from the seeds and beans of soybean, sunflower, safflower, cottonseed, rapeseed (canola) , palm, palmkernel, coconut, corn, evening primrose, borage, groundnut, sesame, and similar, furthermore animal oils and fats such as fish oils, liver oils, egg oils, and similar, obvious to a person skilled in the art, which in combination with the t
  • a preferred aspect of the invention is a food composition wherein the triglyceride oils of the invention are combined with palmkernel oil or coconut oil, giving in addition to a prolonged feeling of satiety also a rapid onset of satiety.
  • the invention also refers to a food composition wherein the galactolipid based emulsifier is a fractionated oat oil.
  • Oil-in-water emulsions refer in this application in addition to liquid oil dispersions also to solid fat dispersions, that is suspensions.
  • Oil-in-water emulsions are prepared by using the emulsifier either alone or in combination with other amphiphilic compounds, such as co-surfactants.
  • the oil-in-water emulsion may also comprise optional additives known in the art for improving different aspects of the composition, such as flavouring agents, sweeteners, colorants, thickening agents, preservatives, antioxidants, etc.
  • Oil-in-water emulsions are prepared by conventional methods. For example, a 30 wt% emulsion of a triglyceride oil in water is prepared by adding the emulsifier to the liquid triglyceride.
  • the continuous phase may be pure water or an aqueous solution containing water-soluble additives such as isotonic agents, sweeteners, flavours, and preservatives. If necessary, the pH of the aqueous phase is then adjusted.
  • the oil phase as well as the aqueous phase are preheated and then the oil phase is added to the aqueous phase under high-shear mixing. The pre-emulsion is then subjected to high-pressure homogenisation.
  • the oily mixture consisting of the triglyceride oils plus the emulsifier may be added to solid or semi-solid foods, which then become naturally emulsified to an oil-in-water emulsion on exposure to the fluids of the gastrointestinal tract.
  • the oily mixture may also contain oil-soluble additives such as antioxidants and flavours.
  • the oily mixture may also be made into a ready-prepared emulsion which can be added to liquid or semi-liquid foods and drinks.
  • the invention especially refers to a food composition wherein the mixture of triglyceride oils and emulsifier or the oil phase of the emulsion comprises 80-99 % by weight of the triglycerides and 1-20 % by weight of emulsifier.
  • the emulsifying capacity of the emulsifier depends on the composition of the emulsifier.
  • the fractionated oat oil mentioned above can without further purification be used as an emulsifier in an amount of 1-20 % by weight of the total composition for preparing oil-in-water emulsions of 5-60 % by weight of triglycerides.
  • the galactolipid emulsifier of WO 95/20943 should be used in 0.1-5.0 % by weight of the total composition for preparing oil-in-water emulsions of 5-80 % by weight of triglycerides.
  • the invention also refers to the use of a mixture of triglyceride oils having a solid fat content at ambient to body temperature and a food emulsifier or an oil-in-water emulsion thereof as a food or for the preparation of a food composition giving a prolonged feeling of satiety, as well as a reduction in calorie intake and especially a selective reduction in fat intake at subsequent meals.
  • the satiety effect is most noticeable during the period 3-4 h after intake.
  • the emulsion or the oily mixture can be used in formulation of dairy products, ice cream, margarines, spreads, salad oils and dressings, processed meat products, confectionery, fillings, sauces, soups, fruit drinks, desserts, baby foods, but also nutritional and pharmaceutical supplements.
  • the oily mixture can be used in solid or semi-solid foods such as chocolates, other candies, baked goods and any other appropriate foods.
  • the invention also refers to a dairy product comprising 1-30 % by weight, preferably 2-15 % by weight of the oil-in- water emulsion.
  • a preferred dairy product such as a yogurt, comprises 4-10 % by weight of an emulsion of a triglyceride fraction of palm oil and fractionated oat oil.
  • a 40 wt% emulsion should be taken in an amount of 1-200 ml per serving or meal, preferably 5-100 ml and very preferably 10-30 ml.
  • the oil component alone that is the oily mixture, may be used in proportionally smaller quantities.
  • the invention also refers to a mixture of triglyceride oils having a solid fat content at ambient to body temperature and a food emulsifier or an oil-in-water emulsion thereof for the preparation of an oral pharmaceutical composition for the prophylaxis and treatment of obesity, for the control of calorie or fat intake and for the prevention and treatment of cardiovascular diseases and diabetes.
  • the invention also refers to the use of an oil-in-water emulsion of triglyceride oils having a solid fat content at ambient to body temperature with a food emulsifier for the preparation of a pharmaceutical composition for the prophylaxis and treatment of obesity, for the control of calorie or fat intake and for the prevention and treatment of cardiovascular diseases and diabetes.
  • the composition When used in a pharmaceutical composition for weight reduction, control of calorie intake or the prevention or treatment of any appropriate disease, such as cardiovascular disease or diabetes, the composition can in addition to the oil- in-water emulsion comprise another therapeutically active substance.
  • Fractionated oat oil (Scotia LipidTeknik, Sweden) comprising about 20 % DGDG, and prepared from oats in accordance with WO 97/11141;
  • Galactolipids (CPL®-Galactolipids, Ontario LipidTeknik, Sweden) comprising about 60 % DGDG, and prepared from oats in accordance with WO 95/20943; soybean lecithin; and soybean phosphatidylcholine.
  • Fractionated palm oil used has the following fatty acid composition as determined by means of gas-liquid chromatography after alkaline ethanolysis : 40-45 wt% palmitic acid, 38-42 wt% oleic acid, 8-10 wt% linoleic acid, and 4-5 wt% stearic acid, the remainder being lauric acid, myristic acid, arachidic acid and palmitoleic acid.
  • the Fractionated palm oil has a triglyceride (TG) content of 99.8-100.0 wt%, a solid fat content at 20 and 35° C (N 20 and N 35 ) of 31 and 6 %, respectively.
  • Example 1 Emulsion giving a prolonged satiety Preparation of 40 wt% emulsions with Fractionated palm oil (batch size 300 g) .
  • the palm oil is melted at 50°C and mixed with the Fractionated oat oil.
  • the oil phase and the water are preheated to 65-70°C and then the oil phase is added to the water under high-shear mixing at 15,000 rpm for 4 min.
  • the pre-emulsion is then divided into two parts; one part is homogenised at 400 bar, the other part at 800 bar, both for 6 cycles at 60°C (Rann- ie homogenizer, Model Mini-Lab 8.30 H, APV Rannie, Denmark). Both parts of the preparation result in emulsions with a similar cream-like consistency.
  • the average particle size (Z average) is in both cases around 480 nm (Zetasizer 4, Malvern Instruments, UK) .
  • An emulsion prepared as above (Olibra®, Ontario LipidTeknik, Sweden) can be stored at 2-8°C until being used as an ingredient in the production of a food product.
  • the Olibra® emulsion can be used as an ingredient in the manufacturing of a yogurt product.
  • a yogurt containing 6-7 % Olibra® is today marketed as Maval® (Skanemejerier, Lunnarp, Sweden) .
  • Example 2 Emulsion giving a prolonged satiety Ingredients wt%
  • the palm oil is melted at 50°C and mixed with the Galactolipids.
  • the oil phase and the water are preheated to 65- 70°C and then the oil phase is added to the water under high- shear mixing at 15,000 rpm for 4 min.
  • the pre-emulsion is homogenised at 800 bar, for 6 cycles at 60°C (Rannie ho o- genizer, Model Mini-Lab 8.30 H, APV Rannie, Denmark). This results in an emulsion with a creamy consistency, with an average particle size (Z average) of 290 nm (Zetasizer 4, Malv- ern Instruments, UK) .
  • Z average average particle size
  • Example 3 Emulsion giving a prolonged satiety Ingredients wt% Water 50.5
  • the palm oil is melted at 50 C C and mixed with the Fractionated oat oil.
  • the oil phase and the water are preheated to 65-70°C and then the oil phase is added to the water under high-shear mixing at 15,000 rpm for 2 min.
  • the pre-emulsion is then homogenised at 600 bar, for 5 cycles at 60°C (Rannie ho o- genizer, Model Mini-Lab 8.30 H, APV Rannie, Denmark). This results in an emulsion with a cream-like consistency.
  • the average particle size (Z average) is ⁇ 400 nm (Zetasizer 4, Malvern Instruments, UK) .
  • Example 4 Emulsion giving a rapid and prolonged satiety Ingredients wt%
  • Fractionated oat oil 2 The palmkernel oil is mixed with the Fractionated palm oil and melted at 65°C and then mixed with the Fractionated oat oil.
  • the water is preheated to 65-70°C and then the oil phase is added to the water under high-shear mixing at 15,000 rpm for 10 min.
  • the pre-emulsion is then homogenised at 600 bar, for 4 cycles at 60 C C (Rannie homogenizer, Model Mini-Lab 8.30 H, APV Rannie, Denmark) . This resulted in an emulsion with a creamlike consistency.
  • the average particle size (Z average) is ⁇ 400 nm (Zetasizer 4, Malvern Instruments, UK).
  • the eggs and the mixture (40:2 by weight) of Fractionated palm oil and Fractionated oat oil are added to the grated carrots and the mixture obtained is whipped by an electric mixer.
  • the batter is poured into a high, oiled and breaded baking-tin and heated for 60 minutes at an oven temperature of 175°C.
  • Test 1 Effect of emulsion on satiety
  • the emulsion prepared in Example 1 at 800 bar was compared to dairy double cream containing 40.0 wt% milk fat, that is the same fat content as Olibra®.
  • 25 ml of the emulsion or the cream were given to five human volunteers instead of a meal at lunch time and swallowed together with 200 ml drinking water. No food or drink was allowed during the following 3 hours.
  • the feeling of satiety or fullness was evaluated every 15 minutes during the first hour and then every 30 minutes using a 100 mm VAS scale (Br. J. Nutr. (1995) 74, 427-436). A value of 100 means a complete satiety and a value of 0 extreme hunger.
  • the results are given in the following table.
  • the emulsion of the invention had a surprising and significantly better effect ( ⁇ 0.05 in paired Student's t test) on satiety compared to the cream.
  • the satiety effect was 20-45 % higher with the emulsion, it was more rapid in onset and lasted longer.
  • Test 2 Stability of different emulsions in gastric juice
  • the stability of emulsions prepared from different oil fractions and different emulsifiers in a simulated gastric environment the following experiment was performed.
  • An emulsion was prepared from 40 % by weight oil or fat, 2 % by weight emulsifier and 58 % by weight water and homogenised at 800 bar in the same way as stated in Example 1.
  • the oils tested were, in addition to the Fractionated palm oil (PO) , Akofrite, that is the non fractionated palm oil, and corn oil (CO) .
  • the emulsifiers were, in addition to the Fractionated oat oil, soybean lecithin (s-lecithin) , and soybean phosphatidylcholine (s-PC) .
  • Test 3 Effect of yogurt containing different fat emulsions on satiety
  • Test 4 Effect of yogurt containing Olibra® on energy intake
  • yogurts had the same energy and macronutrient composition, that is 800 kJ, 6.8 g protein, 28.8 g carbohydrate per portion, and had similar sensory characteristics.
  • control yogurt contained only milk fat, whilst in the test yogurt 5 g of milk fat was replaced by 5 g Olibra®.
  • the test and the control yogurts were supplied by Skanemejerier, Lunnarp, Sweden. After consuming the yogurt, subjects resumed their normal routine for the afternoon, during which period they were instructed not to consume anything other than water, if required. At 17.00 h subjects returned to the Metabolic Suite and were given ad libitum access to a wide range of familiar sweet and savoury foods.
  • N number of subjects not consuming anything after evening meal

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Diabetes (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nutrition Science (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Biophysics (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Edible Oils And Fats (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Confectionery (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Details Of Garments (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Dairy Products (AREA)
PCT/SE1998/001326 1997-07-07 1998-07-06 Satiety product WO1999002041A1 (en)

Priority Applications (19)

Application Number Priority Date Filing Date Title
EP98934040A EP0994655B1 (en) 1997-07-07 1998-07-06 Satiety product
EEP200000011A EE03994B1 (et) 1997-07-07 1998-07-06 Toode täiskõhutunde tekitamiseks
PL338086A PL191304B1 (pl) 1997-07-07 1998-07-06 Środek spożywczy i zastosowanie emulsji typu olej w wodzie zawierającej oleje triglicerydowe
IL13348598A IL133485A (en) 1997-07-07 1998-07-06 A food product that creates a feeling of satiety
KR1020007000090A KR100597221B1 (ko) 1997-07-07 1998-07-06 포만감 생성물
DE69828789T DE69828789T2 (de) 1997-07-07 1998-07-06 Saettigungsgefuehl vermittelndes produkt
AT98934040T ATE287647T1 (de) 1997-07-07 1998-07-06 Saettigungsgefuehl vermittelndes produkt
HU0003122A HU229831B1 (en) 1997-07-07 1998-07-06 Satiety product
EA200000099A EA003833B1 (ru) 1997-07-07 1998-07-06 Пищевая композиция, содержащая эмульсию триглицеридных масел типа "масло-в-воде" и применение эмульсии в качестве пищевого продукта или для приготовления пищевых и фармацевтических композиций
DK98934040T DK0994655T3 (da) 1997-07-07 1998-07-06 Mæthedsprodukt
AU83647/98A AU747540B2 (en) 1997-07-07 1998-07-06 Satiety product
BR9810674-0A BR9810674A (pt) 1997-07-07 1998-07-06 Produto para produzir uma sensação de satisfação do apetite
US09/462,330 US6517883B1 (en) 1997-07-07 1998-07-06 Satiety product
CA002294251A CA2294251C (en) 1997-07-07 1998-07-06 Satiety product
NZ501762A NZ501762A (en) 1997-07-07 1998-07-06 Satiety product comprising triglyceride oils and an emulsifier
JP2000501655A JP3653225B2 (ja) 1997-07-07 1998-07-06 飽満感製品
IS5308A IS5308A (is) 1997-07-07 1999-12-17 Saðningar afurð
NO20000046A NO317044B1 (no) 1997-07-07 2000-01-06 Anvendelse av en olje-i-vann emulsjon for tilveiebringing av en forlenget metthetsfolelse samt for fremstilling av en farmasoytisk sammensetning
HK01102061A HK1031302A1 (en) 1997-07-07 2001-03-21 Satiety product

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9702630A SE9702630D0 (sv) 1997-07-07 1997-07-07 Satiety product
SE9702630-6 1997-07-07

Publications (1)

Publication Number Publication Date
WO1999002041A1 true WO1999002041A1 (en) 1999-01-21

Family

ID=20407678

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SE1998/001326 WO1999002041A1 (en) 1997-07-07 1998-07-06 Satiety product

Country Status (27)

Country Link
US (1) US6517883B1 (ja)
EP (1) EP0994655B1 (ja)
JP (1) JP3653225B2 (ja)
KR (1) KR100597221B1 (ja)
CN (1) CN1094313C (ja)
AT (1) ATE287647T1 (ja)
AU (1) AU747540B2 (ja)
BR (1) BR9810674A (ja)
CA (1) CA2294251C (ja)
CZ (1) CZ298643B6 (ja)
DE (1) DE69828789T2 (ja)
EA (1) EA003833B1 (ja)
EE (1) EE03994B1 (ja)
ES (1) ES2236918T3 (ja)
HK (1) HK1031302A1 (ja)
HU (1) HU229831B1 (ja)
IL (1) IL133485A (ja)
IS (1) IS5308A (ja)
MY (1) MY122266A (ja)
NO (1) NO317044B1 (ja)
NZ (1) NZ501762A (ja)
PL (1) PL191304B1 (ja)
PT (1) PT994655E (ja)
SE (1) SE9702630D0 (ja)
TW (1) TW529912B (ja)
WO (1) WO1999002041A1 (ja)
ZA (1) ZA985943B (ja)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004057982A1 (en) * 2002-12-27 2004-07-15 Ltp Lipid Technologies Provider Ab Food composition comprising a satiety enhancing amount of triacylglycerol and use in the manufacture of a medicament for the treatment or prevention of obesity
WO2007075142A1 (en) * 2005-12-24 2007-07-05 Dsm Ip Assets B.V. Long term weight maintenance
WO2008028994A1 (en) * 2006-09-06 2008-03-13 Cerefi Oy Satiety inducing products and a method of their production
WO2008099025A2 (en) 2007-05-08 2008-08-21 Dsm Ip Assets B.V. Body-weight maintenance and body composition
WO2009144268A1 (en) * 2008-05-30 2009-12-03 Dsm Ip Assets B.V. Composition for increasing gastrointestinal transit time
WO2010112256A1 (en) 2009-04-03 2010-10-07 Dsm Ip Assets B.V. Satiety-inducing composition
WO2011149416A1 (en) 2010-05-24 2011-12-01 Swedish Oat Fiber Ab Aqueous dispersion comprising galactolipids and method for production thereof
US8197842B2 (en) 2003-05-09 2012-06-12 Freedom Health, Llc Dietary supplement and method
WO2019224135A1 (en) * 2018-05-22 2019-11-28 Societe Des Produits Nestle S.A. Powdered beverage comprising glycolipids
WO2021094531A1 (en) * 2019-11-14 2021-05-20 Givaudan Sa Emulsions

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7025984B1 (en) * 2000-06-26 2006-04-11 The Procter & Gamble Company Compositions and methods for body weight management
US20050058671A1 (en) * 2003-05-09 2005-03-17 Bedding Peter M.J. Dietary supplement and method for treating digestive system-related disorders
US7988989B2 (en) * 2003-05-09 2011-08-02 Freedom Health, Llc Nutritional product for enhancing growth and/or strengthening the immune system of equine foals
DE102004043824A1 (de) * 2004-09-10 2006-03-16 Cognis Ip Management Gmbh Emulsionen mit ungesättigten Fettsäuren und deren Estern
AU2005306076B2 (en) * 2004-11-16 2009-08-20 Unilever Plc Satiety emulsions and food compositions
CA2604345A1 (en) * 2005-05-04 2006-11-09 Unilever Plc Satiety emulsions and food compositions
DE102007009029A1 (de) * 2007-02-23 2008-09-04 Südzucker AG Mannheim/Ochsenfurt Niedrig-glykämische Mischungen
US20110052751A1 (en) * 2007-10-10 2011-03-03 Martin Karutz Feed composition for companion animals
US20090123580A1 (en) * 2007-10-17 2009-05-14 Nutracea Methods for treating obesity, insulin resistance and inducing satiety
EP2242375B1 (en) * 2008-01-18 2016-05-18 DSM IP Assets B.V. Spray-dried emulsion
WO2009131436A1 (en) * 2008-04-25 2009-10-29 Campina Nederland Holding B.V. Drinking yoghurt
US8242180B2 (en) * 2008-10-20 2012-08-14 Susan B. Roberts, Llc Use of high satiety, low calorie solid food product in controlling body weight
WO2010107325A1 (en) * 2009-03-17 2010-09-23 Macgibbon Alastair Kenneth Hugh Satiety product
CN102524332A (zh) * 2011-12-19 2012-07-04 北京康比特体育科技股份有限公司 一种减肥压缩饼干及其制备方法
GB2507946A (en) * 2012-09-13 2014-05-21 Inovate Health Ltd Appetite-suppressant composition
CN103315288B (zh) * 2013-03-25 2014-11-05 中国人民解放军总医院 可清洁口腔牙齿的高热量咀嚼片

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987003198A1 (en) * 1985-11-25 1987-06-04 Aco Läkemedel Ab Use of a hydrophobic substance for preparing an enteric preparation for treatment of obesity and an enteric preparation
WO1989002275A1 (en) * 1987-09-03 1989-03-23 New England Deaconess Hospital Corporation Dietary supplement utilizing omega-3/medium chain triglyceride mixtures
EP0465689A1 (fr) * 1990-07-09 1992-01-15 Societe Des Produits Nestle S.A. Composition alimentaire hypocalorique
WO1995020943A1 (en) * 1994-02-04 1995-08-10 Scotia Lipidteknik Ab Oil-in-water emulsions
WO1996010922A1 (de) * 1994-10-05 1996-04-18 Milupa Aktiengesellschaft Phospholipidhaltige fettmischung mit lcp-fettsäuren
WO1997011141A1 (en) * 1995-09-22 1997-03-27 Scotia Lipidteknik Ab Fractionated vegetable oil

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61135572A (ja) * 1984-12-07 1986-06-23 Nippon Oil & Fats Co Ltd 経腸用脂肪乳剤
GB2182942B (en) * 1985-11-15 1989-10-04 Unilever Plc Improvements in and relating to margarine and like fat compositions
US5026548A (en) * 1987-04-28 1991-06-25 Cadbury Schweppes Plc Surfactant
US5258197A (en) * 1989-09-20 1993-11-02 Nabisco, Inc. Reduced calorie triglyceride mixtures
ES2067846T3 (es) * 1990-07-30 1995-04-01 Unilever Nv Crema batible no lactea, basada en aceite liquido.
US5698254A (en) * 1993-01-18 1997-12-16 Unilever Patent Holdings B.V. Coconut cream alternative and method of preparing same
WO1995020945A1 (en) * 1994-02-04 1995-08-10 Scotia Lipidteknik Ab Lipophilic carrier preparations
EP0833570A1 (en) * 1995-06-06 1998-04-08 Campbell Soup Company Therapeutic system for dietary health management
JPH0975001A (ja) * 1995-07-07 1997-03-25 Nisshin Oil Mills Ltd:The 油脂含有飲食物
US6002449A (en) * 1997-10-15 1999-12-14 Zilog, Inc. Integrated television processor
US6229033B1 (en) * 1998-05-11 2001-05-08 E. I. Du Pont De Nemours And Company Fat products from high stearic soybean oil and a method for the production thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987003198A1 (en) * 1985-11-25 1987-06-04 Aco Läkemedel Ab Use of a hydrophobic substance for preparing an enteric preparation for treatment of obesity and an enteric preparation
WO1989002275A1 (en) * 1987-09-03 1989-03-23 New England Deaconess Hospital Corporation Dietary supplement utilizing omega-3/medium chain triglyceride mixtures
EP0465689A1 (fr) * 1990-07-09 1992-01-15 Societe Des Produits Nestle S.A. Composition alimentaire hypocalorique
WO1995020943A1 (en) * 1994-02-04 1995-08-10 Scotia Lipidteknik Ab Oil-in-water emulsions
WO1996010922A1 (de) * 1994-10-05 1996-04-18 Milupa Aktiengesellschaft Phospholipidhaltige fettmischung mit lcp-fettsäuren
WO1997011141A1 (en) * 1995-09-22 1997-03-27 Scotia Lipidteknik Ab Fractionated vegetable oil

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
STN INTERNATIONAL, DERWENT INFORMATION LTD, WPIDS Accession No. 85-014985, "Stable Nutritious Food Compsn. - Comprising Vitamin-E in Phospholipid and Tri Glyceride"; & JP,A,59 210 867 (TAIYO KAGAKU KK) 29-11-84 (8503). *
STN INTERNATIONAL, DERWENT INFORMATION LTD, WPIDS Accession No. 86-202273, "Lipid Emulsion - Comprises Oil Contg. Tri-Saturated Glyceride and Palmitic Acid, Water and Emulsifier"; & JP,A,61 135 572 (NIPPON OILS & FATS CO LTD) 23-06-86 (8631). *
STN INTERNATIONAL, DERWENT INFORMATION LTD, WPIDS Accession No. 93-330535, "Oil-in-Water Type Emulsion for Whipping Cream - Contains Tri Glyceride Contg. (Un)satd. Fatty Acid Residue(s), Emulsifier, Milk Protein and Flavour Improver"; & JP,A,05 236 898 (KAO CORP) 17-09-93 (9342). *
STN INTERNATIONAL, DERWENT INFORMATION LTD, WPIDS Accession No. 94-147852, "Emulsion for Treating Diabetes with Immediate Effect - Contg. Tri Glyceride of 4,7,10,13,16,19-Docosa Hexa Enoic Acid"; & JP,A,06 092 848 (SAGAMI CHEM RES CENTRE) 05-04-94 (9418). *
STN INTERNATIONAL, DERWENT INFORMATION LTD, WPIDS Accession No. 94-363533, "Agent for Preventing and/or Therapeutics of Alzheimer's Disease - Contg. Tri Glyceride of 8-10 Carbon Fatty Acids as Active Ingredient"; & JP,A,06 287 138 (GREEN CROSS CORP) 11-10-94 (9445). *
STN INTERNATIONAL, DERWENT INFORMATION LTD, WPIDS Accession No. 97-239185, "Foods and Drinks Containing Oil and Fat - Contain Tri Glyceride Mixture for High Accumulation of Docosa-Hexa Enoic Acid"; & JP,A,09 075 001 (NISSHIN OIL MILLS LTD) 25-03-97 (9722). *
STN INTERNATIONAL, DERWENT INFORMATION LTD, WPIDS Accession No. 98-012224, "Foaming Oil-in-Water Type Emulsified Matter, used as Topping or Filling for Bread or Cakes - Comprises Fat, Protein, Emulsifier, Saccharide(s) and/or Sugar Alcohol and Water"; & JP,A,09 275 923 (KAO CORP) 28-10-97 (9802). *

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004057982A1 (en) * 2002-12-27 2004-07-15 Ltp Lipid Technologies Provider Ab Food composition comprising a satiety enhancing amount of triacylglycerol and use in the manufacture of a medicament for the treatment or prevention of obesity
US8197842B2 (en) 2003-05-09 2012-06-12 Freedom Health, Llc Dietary supplement and method
EP1981490A4 (en) * 2005-12-24 2013-01-09 Dsm Ip Assets Bv LONG TERM WEIGHT MAINTENANCE
WO2007075142A1 (en) * 2005-12-24 2007-07-05 Dsm Ip Assets B.V. Long term weight maintenance
US8329759B2 (en) 2005-12-24 2012-12-11 Dsm Ip Assets B.V. Long term weight maintenance
EP1981490A1 (en) * 2005-12-24 2008-10-22 DSMIP Assets B.V. Long term weight maintenance
EP2068663A4 (en) * 2006-09-06 2011-01-19 Cerefi Oy PRODUCTS FOR ENHANCING SATIETY SENSATION AND PROCESS FOR PRODUCING THE SAME
US8962046B2 (en) 2006-09-06 2015-02-24 Teknologian Tutkimuskeskus Vtt Satiety inducing products and a method of their production
EP2068663A1 (en) * 2006-09-06 2009-06-17 Cerefi Oy Satiety inducing products and a method of their production
WO2008028994A1 (en) * 2006-09-06 2008-03-13 Cerefi Oy Satiety inducing products and a method of their production
WO2008099025A3 (en) * 2007-05-08 2008-10-02 Dsm Ip Assets Bv Body-weight maintenance and body composition
WO2008099025A2 (en) 2007-05-08 2008-08-21 Dsm Ip Assets B.V. Body-weight maintenance and body composition
WO2009144268A1 (en) * 2008-05-30 2009-12-03 Dsm Ip Assets B.V. Composition for increasing gastrointestinal transit time
US8952063B2 (en) 2009-04-03 2015-02-10 Dsm Ip Assets B.V. Satiety-inducing composition
US8530514B2 (en) 2009-04-03 2013-09-10 Dsm Ip Assets B.V. Satiety-inducing composition
WO2010112256A1 (en) 2009-04-03 2010-10-07 Dsm Ip Assets B.V. Satiety-inducing composition
WO2011149416A1 (en) 2010-05-24 2011-12-01 Swedish Oat Fiber Ab Aqueous dispersion comprising galactolipids and method for production thereof
US9237762B2 (en) 2010-05-24 2016-01-19 Swedish Oat Fiber Ab Aqueous dispersion comprising galactolipids and method for production thereof
WO2019224135A1 (en) * 2018-05-22 2019-11-28 Societe Des Produits Nestle S.A. Powdered beverage comprising glycolipids
WO2021094531A1 (en) * 2019-11-14 2021-05-20 Givaudan Sa Emulsions

Also Published As

Publication number Publication date
EP0994655A1 (en) 2000-04-26
PL191304B1 (pl) 2006-04-28
HK1031302A1 (en) 2001-06-15
TW529912B (en) 2003-05-01
ZA985943B (en) 1999-01-28
CZ298643B6 (cs) 2007-12-05
AU747540B2 (en) 2002-05-16
AU8364798A (en) 1999-02-08
SE9702630D0 (sv) 1997-07-07
HUP0003122A3 (en) 2001-03-28
IL133485A0 (en) 2001-04-30
PL338086A1 (en) 2000-09-25
EA003833B1 (ru) 2003-10-30
KR100597221B1 (ko) 2006-07-11
NO317044B1 (no) 2004-07-26
CN1094313C (zh) 2002-11-20
BR9810674A (pt) 2000-09-26
ES2236918T3 (es) 2005-07-16
PT994655E (pt) 2005-05-31
US6517883B1 (en) 2003-02-11
HU229831B1 (en) 2014-09-29
DE69828789T2 (de) 2006-04-06
EP0994655B1 (en) 2005-01-26
EA200000099A1 (ru) 2000-08-28
NO20000046D0 (no) 2000-01-06
NO20000046L (no) 2000-03-02
JP3653225B2 (ja) 2005-05-25
IS5308A (is) 1999-12-17
KR20010021532A (ko) 2001-03-15
HUP0003122A2 (hu) 2001-02-28
ATE287647T1 (de) 2005-02-15
JP2001509364A (ja) 2001-07-24
DE69828789D1 (de) 2005-03-03
CA2294251C (en) 2003-12-23
MY122266A (en) 2006-04-29
CA2294251A1 (en) 1999-01-21
NZ501762A (en) 2001-12-21
EE03994B1 (et) 2003-04-15
CZ468899A3 (cs) 2000-04-12
IL133485A (en) 2004-02-19
CN1268869A (zh) 2000-10-04
EE200000011A (et) 2000-08-15

Similar Documents

Publication Publication Date Title
US6517883B1 (en) Satiety product
CA2396071A1 (en) Thickened oil compositions of edible oil
JP2012522737A (ja) 満腹誘発組成物
JP2004534793A (ja) 安定化されたフィトステロールの油中分散液
US20090317509A1 (en) Satiety emulsions and food compositions
JP5707026B2 (ja) 長期体重維持
JP4687863B2 (ja) リン脂質含有の安定なマトリックスを含んでいる機能食品
US20100261790A1 (en) Body-weight maintenance and body composition
Ferrari MODELLING THE PERFORMANCES OF TRADITIONAL AND INNOVATIVE FATS IN A PLUM CAKE FORMULATION
MXPA00000349A (en) Satiety product
Miele Novel approaches in healthy cream development: oleogels and a natural sweetener
FERRARI Facoltà di Agraria
WO2009144268A1 (en) Composition for increasing gastrointestinal transit time

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 133485

Country of ref document: IL

Ref document number: 98806927.X

Country of ref document: CN

AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH GM GW HR HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 501762

Country of ref document: NZ

ENP Entry into the national phase

Ref document number: 2294251

Country of ref document: CA

Ref document number: 2294251

Country of ref document: CA

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: PV1999-4688

Country of ref document: CZ

WWE Wipo information: entry into national phase

Ref document number: 1998934040

Country of ref document: EP

Ref document number: 1020007000090

Country of ref document: KR

Ref document number: 09462330

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: PA/a/2000/000349

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 83647/98

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 200000099

Country of ref document: EA

WWP Wipo information: published in national office

Ref document number: PV1999-4688

Country of ref document: CZ

WWP Wipo information: published in national office

Ref document number: 1998934040

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWP Wipo information: published in national office

Ref document number: 1020007000090

Country of ref document: KR

WWG Wipo information: grant in national office

Ref document number: 83647/98

Country of ref document: AU

WWG Wipo information: grant in national office

Ref document number: 1998934040

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1020007000090

Country of ref document: KR

WWG Wipo information: grant in national office

Ref document number: PV1999-4688

Country of ref document: CZ